4-(4-Chlorophenoxy)benzene-1-sulfonyl chloride → HCID 59467988, compound

HRID 1716303Notes

Reaction equation

HRID 1716303 reaction equation
Br.[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]1=[O:17].[Cl:18][C:19]1[CH:35]=[CH:34][C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[CH:21][CH:20]=1>C(Cl)Cl.O>[CH2:10]([O:9][N:5]1[CH2:6][CH2:7][CH2:8][C@@H:3]([NH:2][S:30]([C:27]2[CH:28]=[CH:29][C:24]([O:23][C:22]3[CH:34]=[CH:35][C:19]([Cl:18])=[CH:20][CH:21]=3)=[CH:25][CH:26]=2)(=[O:31])=[O:32])[C:4]1=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 27577504-(4-Chlorophenoxy)benzene-1-sulfonyl chlorideHCID 68518813HCID 68518813, compound

Product 1

HCID 59467988HCID 59467988, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of (R)-3-amino-1-benzyloxy-piperidin-2-one hydrogen bromide salt (0.086 g, 0.29 mmol) (synthesized according to Miller's procedure J. Org. Chem. 2002, 67, 4759) and 4-(4-chloro-phenoxy)-benzenesulfonyl chloride (0.095 g, 0.31 mmol) in dry CH2Cl2 (3 mL) was treated with TEA (0.12 mL, 0.86 mmol) under N2. The reaction mixture was stirred at room temperature for 6 h and diluted with CH2Cl2 and water. After the usual work-up, the crude material was purified by chromatography (silica gel, 35% EtOAc/hexanes) to give the desired product, (R)—N-(1-Benzyloxy-2-oxo-piperidin-3-yl)-4-(4-chloro-phenoxy)-benzene-sulfonamide. MS (EI) 487 (M+H)+.

Workup

  1. customAfter the usual work-up, the crude material was purified by chromatography (silica gel, 35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d57a67655e1d4969859a57de19b38b08
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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